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Unexpected regioselectivities of [3 + 2] cycloaddition of azomethine imines to acrylonitrile and 4-nitrophenyl vinyl sulfone

Mikhail Igorevich Pleshchev 1
Mikhail Igorevich Pleshchev
, 
Vadim Vadimovich Kachala 1
Vadim Vadimovich Kachala
, 
Alexander Sergeyevich Goloveshkin 2
Alexander Sergeyevich Goloveshkin
, 
Ivan Sergeevich Bushmarinov 2
Ivan Sergeevich Bushmarinov
, 
Vladimir Vladimirovich Kuznetsov 1
Vladimir Vladimirovich Kuznetsov
, 
Dmitry Victorovich Khakimov 1
Dmitry Victorovich Khakimov
, 
Nina Nikolaevna Makhova 1
Nina Nikolaevna Makhova
10.1016/j.mencom.2013.09.011
Published 2013-09-10
Communication , Volume 23, Issue 5, 271-273
24
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Pleshchev M. I. et al. Unexpected regioselectivities of [3 + 2] cycloaddition of azomethine imines to acrylonitrile and 4-nitrophenyl vinyl sulfone // Mendeleev Communications. 2013. Vol. 23. No. 5. pp. 271-273.
GOST all authors (up to 50) Copy
Pleshchev M. I., Kachala V. V., Goloveshkin A. S., Bushmarinov I. S., Kuznetsov V. V., Khakimov D. V., Makhova N. N. Unexpected regioselectivities of [3 + 2] cycloaddition of azomethine imines to acrylonitrile and 4-nitrophenyl vinyl sulfone // Mendeleev Communications. 2013. Vol. 23. No. 5. pp. 271-273.
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TY - JOUR
DO - 10.1016/j.mencom.2013.09.011
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.09.011
TI - Unexpected regioselectivities of [3 + 2] cycloaddition of azomethine imines to acrylonitrile and 4-nitrophenyl vinyl sulfone
T2 - Mendeleev Communications
AU - Pleshchev, Mikhail Igorevich
AU - Kachala, Vadim Vadimovich
AU - Goloveshkin, Alexander Sergeyevich
AU - Bushmarinov, Ivan Sergeevich
AU - Kuznetsov, Vladimir Vladimirovich
AU - Khakimov, Dmitry Victorovich
AU - Makhova, Nina Nikolaevna
PY - 2013
DA - 2013/09/10
PB - Mendeleev Communications
SP - 271-273
IS - 5
VL - 23
ER -
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@article{2013_Pleshchev,
author = {Mikhail Igorevich Pleshchev and Vadim Vadimovich Kachala and Alexander Sergeyevich Goloveshkin and Ivan Sergeevich Bushmarinov and Vladimir Vladimirovich Kuznetsov and Dmitry Victorovich Khakimov and Nina Nikolaevna Makhova},
title = {Unexpected regioselectivities of [3 + 2] cycloaddition of azomethine imines to acrylonitrile and 4-nitrophenyl vinyl sulfone},
journal = {Mendeleev Communications},
year = {2013},
volume = {23},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.09.011},
number = {5},
pages = {271--273},
doi = {10.1016/j.mencom.2013.09.011}
}
MLA
Cite this
MLA Copy
Pleshchev, Mikhail Igorevich, et al. “Unexpected regioselectivities of [3 + 2] cycloaddition of azomethine imines to acrylonitrile and 4-nitrophenyl vinyl sulfone.” Mendeleev Communications, vol. 23, no. 5, Sep. 2013, pp. 271-273. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.09.011.

Abstract

The [3 + 2] cycloaddition of azomethine imines derived from 6-aryl-1,5-diazabicyclo[3.1.0]hexanes to acrylonitrile and 4-nitrophenyl vinyl sulfone proceeds with high diastereoselectivity, but with opposite regioselectivity, which has been clarified by quantum chemical calculations.

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